


One of These Nights

by TheGreatDivide



Series: Cinnamon Whiskey - Dean and Cheyenne [2]
Category: Supernatural
Genre: College, Confessions, Cute, Dean Winchester Can't Say "I Love You", Drinking, F/M, Fluff
Language: English
Status: Completed
Published: 2018-12-21
Updated: 2018-12-21
Packaged: 2019-09-24 08:14:27
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,136
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17097089
Author URL: https://archiveofourown.org/users/TheGreatDivide/pseuds/TheGreatDivide
Summary: Dean and Cheyenne go to the bar with some of her College friends, and given their track record with her ex-boyfriends, it goes about as well as expected.





	One of These Nights

**Author's Note:**

  * Inspired by [Cinnamon Whiskey](https://archiveofourown.org/works/15628335) by [TheGreatDivide](https://archiveofourown.org/users/TheGreatDivide/pseuds/TheGreatDivide). 



> This idea was sent to me by one of the readers of Cinnamon Whiskey from where I have it posted on quotev.com. It's set in the early chapters of Cinnamon Whiskey, while Cheyenne is still attending college, but knows about Dean's job.

 

"You know what, maybe this isn't such a good idea." Dean said suddenly, coming to an abrupt stop outside the door to the bar. Cheyenne turned on her heel slowly to look back at him, pursing her lips in frustration. 

"This was  _your_  idea."

"Well why did you choose  _now_  to start listening to me?" Dean hissed defensively, glancing around the almost deserted street as if he was looking for an escape route. Cheyenne couldn't understand why he was so nervous about this; after all, he saw Ana every time he was in the apartment, and he'd already meet Jake and George once before when he'd picked her up from the bar almost a month earlier. In fact, when she'd told him she was going out for drinks that afternoon, he'd been the one to suggest that he tagged along and got to know them better. Why was he being so difficult now?

"How about I just go back to your apartment and then come back and pick you up later?" He suggested. "The last Hunt was a pain in the ass, I'm  _really_  tired..."

"Didn't seem all that tired two hours ago." She pointed out, cocking an eyebrow as she folded her arms. Dean paused to consider that, barely concealing a smirk as he thought about it. Yeah, she had a point. 

Cheyenne took his moment of distraction to grab him by the forearm and drag him inside the bar after her, knowing it would be a lot harder for Dean to walk out  _after_  her friends had seen him. Sure enough, they'd only made it a few feet in before Ana spotted them, waving them over to the table. 

Dean was wary of this group of virtual strangers. They seemed nice enough, and he knew Cheyenne loved them, but if he was honest,  _he_ was a Hunter, and  _they_  were College students. Not really the most likely recipe for a great night out. Nonetheless, when Cheyenne let go of his arm to hug Ana and Jake, he relaxed just a little. It was good to see her like this, with that grin that stretched across her face until her eyes crinkled at the corners. Since the hunt with McGinley, he hadn't really seen that grin, and he'd missed it. 

They'd chosen the table tucked into the back of the bar where it was a little quieter, not far from where he and Cheyenne had sat on their first date. In fact, when Dean eased himself into the booth beside Cheyenne and craned his neck a little, he could see the table they'd sat at. 

Even though they'd all been talking before he and Cheyenne had walked in, as soon as they sat down Dean noticed the table fell silent. George and Jake shot him slightly suspicious glances that they didn't think he'd notice in the dim lighting, neither one entirely comfortable with his presence. Not that he blamed them; Cheyenne had already (jokingly) informed him that he gave off a -don't-fuck-with-me vibe that could be sensed a mile away, and Jake was naturally nervous of people who could beat the shit out him without breaking a sweat. 

"So..." He broke the uncomfortable silence, drumming his fingers against the bar. "Drinks. What are we having?"

The guys both asked for beers, Ana ordered a Gin and Tonic, and Cheyenne just shrugged and told him to surprise her, shooting him a teasing grin as he stood up and walked to the bar. Almost as soon as he'd gotten up from the table, Dean could hear light chatter start up, and winced involuntarily. 

He'd been the new kid in class more times than he could count. He'd drifted from school to school, making acquaintances that sometimes called him a friend before the first day was over, but for some reason that he couldn't put his finger on, he was struggling here. He felt awkward and uncomfortable and out of place, like he was wearing a neon sign around his neck that screamed  _I Do Not Belong_. It was an unfamiliar sensation, and it wasn't one he liked. 

Dean had been stood at the bar for a few minutes before Cheyenne joined him, leaning into him and grinning up at him in an attempt to elicit a smile, or any kind of reaction. "You okay, grumpy?"

He managed a small smile for her, nodding. "Absolutely."

"You know, for a professional liar, you  _really_  suck at it." She teased, sliding her hand over his forearm soothingly for a few seconds. It worked just as well as she'd hoped, and after a moment Dean's shoulders relaxed a little under his heavy leather jacket. "Just chill out a little, okay? Be yourself."

"I don't think your friends want me there." He pointed out quietly. "Ana might, but the other two don't."

Cheyenne laughed gently. "Yeah, there's a reason for that. I mean, have you  _seen_  you? Jesus, Dean - if I were a guy,  _I'd_  be threatened by you!"

He shrugged lamely, avoiding her gaze until she nuzzled up to him, that teasing grin from before still on her lips. "They're just trying to test your resolve a little, feel you out. They did this with my ex-boyfriend too." 

"So I'm getting subjected to the human lie detector test?" He shot back, cocking an eyebrow as three beers were placed in front of him. "Sounds like a fun evening."

Cheyenne decided to change her tactic a little. Supporting him clearly wasn't working, so instead she resorted to bribery, cooing his name as she leaned in closer, her voice dripping with suggestion. "If you get through the whole night,  _I'll make it up to you tomorrow_."

Dean groaned low in his throat at that promise, and gave out against his better judgement. "Fine.  _Fine_. But you'd better be naked all day tomorrow."

Cheyenne laughed at that, kissing his cheek gently and taking the beers. "I will be, don't worry."

"I mean ass-naked." He reiterated. "No clothes. All day." 

"Alright!" She laughed, shaking her head as she walked back to the table with the beers, handing one to Jake, one to George and leaving the last one for him. Dean watched her go, smiling gently as she slid into the booth and started talking to her friends again, throwing her head back with laughter at something Jake said. Tonight was probably going to be slow and painful, but if Dean was totally honest with himself, it was worth it just to hear that laugh. 

He walked over to the table with the last two drinks in hand a few minutes later, and thankfully this time the conversation didn't end abruptly with his arrival. Ana accepted her drink gratefully, while Cheyenne sniffed hers suspiciously. "Cinnamon Old Fashioned?"

"Bingo." He smiled gently, draping one arm over the back of the booth and letting his fingertips dance over her shoulder. 

"Good choice." She smiled, leaning into him a little bit as Ana and Jake started talking about something that had happened earlier in class. For the most part, Dean just sat there and listened, occasionally interjecting with a question or two, but otherwise just letting the conversation wash over him while Cheyenne cuddled up to his side. Ana and Jake seemed more than happy to fill him in on all of the campus gossip, while George largely ignored him, which suited Dean just fine. 

They'd been sat at the bar for almost an hour, and had gone through three rounds before Cheyenne started to ease herself out of the booth, excusing herself as she stood up. "Bathroom break. Play nicely while I'm gone, kids." 

The comment was general, but her tone was pointed, and when Cheyenne spoke she looked directly at Ana, who responded with an innocent enough grin. "We always do."

She'd barely made it ten feet from the table before Ana's grin twisted into something that probably should have scared Dean, and she slid into the seat next to him. "So, Dean. Let's talk about you and my best friend."

Dean bit back the exasperated groan that rose from deep in his throat, and resisted the urge to roll his eyes. So Cheyenne had been right - Ana was about to grill him. "I thought she told you to play nicely." 

The two men seemed to have perked up at the chance to ask invasive questions at Dean's expense, and leaned in conspiratorially. The three of them exchanged grins, and Ana leaned a little closer. "There's a queue for the toilets. We've got plenty of time."

He groaned internally.  _Fantastic._

"So, let's get started, Winchester." Ana took a sip of her drink, but before she could begin, Jake blurted out (what he assumed was) an embarrassing first question, garbling the words a little.

"So have you had sex yet?"

Slowly, Ana, George and Dean all turned to face him, equally confused. Jake's cheeks flushed a little as he looked between them, shrugging lamely. "What? I just thought, because it took her and Marcus so long to-"

"Dude, they've been together for six months." George said quietly, shaking his head slowly. "Of  _course_  they've had sex."

"They had sex on the first date." Ana pointed out, smirking. Two sets of surprised eyes landed on Dean, and when he looked from Ana to Jake and George, he couldn't help but snort. George's eyebrows had shot for his hairline, and Jake's mouth hung open a little in shock. 

"The first night?" He echoed quietly. Dean couldn't help but laugh at his reaction. 

"Yeah, I thought she'd have told you."

"Well she  _didn't_!" If Dean didn't know any better, he'd have said Jake actually seemed a little offended that he'd been kept out of the loop. 

"I've got to say, it took me by surprise too." Ana admitted. "Random one night stands aren't really Cheyenne's style. But  _anyway_. I don't care about your sex life, I hear enough of it through the apartment walls as it is. What  _I_  want to know is whether you're good enough for my best friend."

He smiled gently at her protectiveness, taking a sip of his beer. "Okay, shoot." 

"Ever been married?"

"Fuck no." He laughed. It might not have been the right response, because Dean saw Ana's eyes narrow a little in suspicion. 

"When was your last serious relationship?" She asked slowly. Dean met her gaze over the top of his beer bottle, smiling softly. 

"Define serious?"

"Longer than four months." George offered. 

"Oh, then this is my first."

That took them all by surprise, and Dean caught them shooting uncertain glances at each other over the table. "You're what... twenty five and you've never been in a serious relationship?"

"No," He corrected gently, "I've been in  _one_  serious relationship."

Ana didn't really know how to respond to that, and fell silent. George asked the next question. "Ever cheated?"

"Once. I was in high school, seeing two girls at the same time." He winced involuntarily at the memory. "Not my proudest moment." 

"Good." George retorted, sipping his own beer as he waited for someone else to ask a question. Ana was the one to ask it. 

"What's your favourite thing about her?"

He had to think about that for a second, looking off into middle distance as he pictured her stood in front of him. He pictured her eyes, saw them crinkling in the corners and twinkling in the light. He heard her laugher like she was right beside him, heard how warm it was, how full of life. Every time he heard it, no matter how tired he was, no matter how bloodied and beaten from a job, that laugh never failed to make Dean smile. That was what he settled on, and that was what he told them, his voice soft and barely carrying over the chatter of the bar. 

Ana paused, glancing between Jake and George before she asked the next question, a little hesitant when she spoke. "Do you love her?"

Dean's head snapped around to look at her so quickly it almost made her jump. The question had taken him by surprise, and for a few seconds Dean was so stunned that he couldn't even speak, he just stared at her in silence while he tried to form words - any words. "I... I-"

He didn't get the chance to answer, because Cheyenne reappeared at that moment, dropping into the space next to Dean. "I'm back! The queue is insane, I hope no-one else needs to go."

Ana moved back to her own seat, grinning to herself. Dean hadn't answered, not verbally at least, but those few seconds of stunned silence were all she needed, especially when she saw the way he looked at her when she got back. 

"Nope." She smiled over at her best friend. "I'm fine."


End file.
